The production of an alcohol and/or a ketone from a corresponding alkene by a gas phase reaction in the presence of water vapor includes, for example, the production of acetone from propylene, the production of methyl ethyl ketone (MEK) from 1-butene or 2-butene, the production of cyclohexanone from cyclohexene and the production of tert-butanol from isobutene. All of these products are industrially very important chemical substances as chemical starting materials or solvents.
As prior art reactions as the above-mentioned reaction, there are mainly exemplified a Wacker type reaction using a noble metal catalyst such as a palladium compound, and a reaction using a compound oxide catalyst of metals other than noble metals, such as molybdenum, tungsten, tin, cobalt and the like.
As an example of process in which the former reaction, i.e., the Wacker type reaction is carried out, there is a process in which a carbonyl compound is produced in the presence of an olefin, oxygen and water vapor by the use of a catalyst obtained by supporting palladium and/or a palladium compound and copper chloride on a carrier such as silica, alumina or the like (see, for example, JP-A-49-72209). The working example of JP-A-49-72209 discloses the production of methyl ethyl ketone (MEK) from 1-butene by the use of a catalyst obtained by supporting palladium chloride and copper chloride on silica.
In addition, as an example of process not using a chloride as a catalyst, there is a process in which a catalyst obtained by supporting a palladium salt and a vanadyl salt on active carbon is used for producing acetaldehyde or a ketone by subjecting an olefin to vapor phase oxidation with oxygen or an oxygen-containing gas in the presence of water vapor (see, for example, JP-A-59-163335). The working example of JP-A-59-163335 discloses the production of acetone from propylene by the use of a catalyst obtained by supporting palladium sulfate and vanadyl sulfate on active carbon.
These catalysts, however, are obtained by the use of the very expensive noble metal. Moreover, as a result of repeat experiment by the present inventors, it was found that both of the catalysts were deteriorated in activity in a short time.
As an example of process in which the latter reaction using no noble metal catalyst is carried out, there is a process in which an olefin is reacted with oxygen in the presence of water vapor by the use of a catalyst comprising molybdenum oxide and close-grained tin oxide uniformly distributed on a carrier (see, for example, JP-B-47-8046). The working example of JP-B-47-8046 discloses the production of acetone from propylene by the use of a catalyst obtained by supporting tin dioxide and molybdenum trioxide on silica.
As an example of process using a similar catalyst, there is a process in which a mixture of an olefin and water vapor is subjected to reaction by the use of a catalyst obtained by supporting molybdenum oxide, tin oxide and a specific amount of an alkali metal and/or an alkaline earth metal on a carrier (see, for example, JP-A-49-61112). The working example of JP-A-49-61112 discloses the production of MEK from trans-butene by the use of a catalyst obtained by supporting tin dioxide, molybdenum trioxide and sodium on silica.
In addition, there is a process in which a similar catalyst is used and a gas as starting material for reaction comprising an olefin, water vapor and a small amount of oxygen and a gas containing a large amount of oxygen are alternately brought into contact with the catalyst (see, for example, JP-B-49-34652). The working example of JP-B-49-34652 discloses the production of MEK from n-butene by the use of a catalyst obtained by supporting tin dioxide and molybdenum trioxide on silica.
However, as a result of repeat experiment by the present inventors, all of these processes using a catalyst comprising metals other than noble metals were found to be disadvantageous in that the selectivity of a ketone as a desired product obtained from an alkene fed is lowered because a very large amount of carbonaceous substances are produced on the catalyst by the reaction.